Sailing BC’s Gulf Islands: Why This Became Our Family’s Best Trip Ever

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It was our last evening on the water after a week of sailing BC’s Gulf Islands. Brentwood Bay Resort, an oceanfront table, the Gulf Islands going dark around us. Tracy Sarich and Paul Miller — the founder and lead instructor of Voyage Makers Coastal Adventures, who had sailed with us all week — were asking the question every good host eventually asks: what was the best trip you had ever taken? I have been to French Polynesia. I have spent months in Australia. I have driven every major highway in Canada and called it professional research. I said THIS ONE. I meant it without hesitation.

That is a significant claim for a travel writer. It is an even more significant claim from a travel writer who runs a road-trip publication — not a sailing magazine, not a coastal-lifestyle brand — and who arrived at Port Sidney Marina on a Friday afternoon having never sailed.. Adventure Awaits is built on road trips. We know cars, highways, provincial parks, and the particular joy of pulling into a small town at golden hour and finding something worth writing about. This was different. This was six days aboard Simply Dreaming, a 45-foot Catalina, sailing BC’s Gulf Islands with my family. And it became the best trip we have ever taken.

What made it that way is not one thing. It is Robin McKeown, founder of Seaport Yacht Charters, who built her company on the conviction that a great charter experience begins before you hand someone a key. It is Tracy Sarich, who designed our week around a teaching philosophy called the Skipper’s Mindset and matched us with an instructor from Tasmania named Paul Miller. It was our Captain who is, without qualification, one of the best teachers I have encountered in any context. It is my son finding the helm on Day 1 and not wanting to leave it for the rest of the week. It is my daughter bringing a 45-foot boat into a marina berthin between two super yachts, all while a dock worker looked on in disbelief. (and me, a proud Mom, glowing) And it is an orca, surfacing less than 100 feet from shore on our very first night in port, as if the Gulf Islands wanted to make sure we understood exactly what we had arrived at.

This article is the story of that week and the companies that made it possible. It is also the map to two companion pieces that go deeper: the Seaport Yacht Charters feature, which covers the boat, the charter experience, and Robin’s extraordinary company, and the Voyage Makers feature, which covers the week of sailing instruction, Paul’s teaching, and what a family of four who had never sailed before looks like by the end of five days with the right instructor. If you are a family considering a sailing charter in BC, someone who has always wanted to learn to sail, or simply a person wondering whether the Gulf Islands deserve their reputation — the short answer is yes. Enthusiastically, unequivocally yes.

Quick Trip Overview

Cockpit view on a sailboat with navigation screen displaying nautical chart, speed, depth, and heading
Destination:BC’s Southern Gulf Islands
Departure Point:Port Sidney Marina, Sidney, BC
Charter Company:Seaport Yacht Charters (proudly Canadian, female-owned)
Sailing Instruction:Voyage Makers Coastal Adventures (proudly Canadian, female-owned)
Vessel:Simply Dreaming (45-foot Catalina, 3 staterooms, 2 heads)
Itinerary:Port Sidney → Montague Harbour → Ganges → Genoa Bay → Brentwood Bay → Port Sidney
Trip Length:6 days/5 nights
Best Time to Visit:May through September; peak season June through August
Experience Required:None — instructional charter option available through Voyage Makers partnership

The Companies Behind the Week

Seaport Yacht Charters: Your Adventure, Thoughtfully Delivered

Robin McKeown in blue anchor-patterned shirt and white capris on a white sailboat named "Simply Dreaming" with a life preserver
Robin McKeown smiling on a boat with a Canadian flag, other boats in background

Seaport Yacht Charters is a proudly Canadian, female-owned company founded by Robin McKeown in January 2026 — which sounds new until you understand that Robin brought 25 years of marine industry experience to it. She was the first woman in Canada to receive the Certified Marine Manager designation in 2018. As of this writing, there are approximately four women in Canada who hold it. Robin is known in the industry for the people she mentors: the new marina manager at Port Sidney Marina completed his CMM with Robin as his referring CMM holder, and that kind of chain — professionals investing in the next generation of professionals — is what Robin calls the point of the credential.

Her office is on the dock at Port Sidney Marina, steps from the fleet. When she walked us to Simply Dreaming on arrival day, we found a welcome card printed with every family member’s name, a bouquet of boat-friendly flowers, and cookies from The Fickle Fig bakery in Sidney, a special treat that made the boat instantly feel like home. The snickerdoodle cookies were gone before the first night was out. The boat itself — a 45-foot Catalina with three staterooms and two full heads — was so far beyond the photos on the website that I genuinely did not know what to say when we walked down into the galley. It was, in every sense, more than I had imagined.

Voyage Makers Coastal Adventures: The Coast Changes You

Tracy Sarich smiling, in a dark blue shirt and blue pants, standing in front of the Voyage Makers Coastal Adventures office
Tracy Sarich steering a sailboat in a harbor with green hills under a partly cloudy sky

Voyage Makers Coastal Adventures was founded by Tracy Sarich, and her origin story sounds too good to be true until you meet her and realize it is also accurate. She worked at Amazon, went to law school, clerked for a judge, discovered sailing, and eventually sold her Seattle house and car — ‘all we had,’ she told us at dinner on our last night, ‘was a Vespa and a boat’ — with every intention of going offshore. COVID grounded the plan. She started teaching instead. Voyage Makers is what she built from that pivot: a proudly Canadian, female-owned sailing school with no fixed fleet, a regional operating model, and a teaching framework called the Skipper’s Mindset built on the conviction that confidence is the real curriculum.

Our instructor, Paul Miller, is originally from Tasmania and has been sailing for more than 20 years across BC, New Zealand, and the Sea of Cortez. He arrived Saturday morning, read the family dynamic within ten minutes, and spent the week calibrating his instruction to four completely different learners simultaneously without making any of it feel like a process. Tracy put it simply when she explained why she had matched him to us: this is what the man was born to do.

The Moments That Made It

Night One: An Unexpected Guest

Sailing BC’s Gulf Islands - Orca dorsal fin in blue water with islands and sky in background
Sailing BC’s Gulf Islands - Orca dorsal fin in blue water with islands and sky in background

We arrived in Sidney on the afternoon ferry, had dinner at Jack’s On The Water with a view straight over the marina, and walked back to the boat along the waterfront. My daughter said: ‘Mom, there’s a whale.’ I told her there wasn’t. Then the dorsal fin broke the surface. We were on foot, on a coastal path, under 100 feet from the water — close enough to watch an orca clearly, which under BC’s on-water regulations is an uncommon privilege. We stood there until she swam away, and for a moment afterward nobody said anything. Then someone said what we were all thinking: we are somewhere genuinely, startlingly special. It was the first night. It was exactly the right omen.

The Boat

White sailboat "Simply Dreaming" with blue stripe and dinghy on grey water, cloudy sky, wooded islands and other boats in background

I had seen the photos of Simply Dreaming before we arrived. I thought I knew what to expect. I was wrong. The boat was larger, more beautiful, and more genuinely liveable than any image suggested. Three proper staterooms. Two full heads with showers. A galley where you could actually cook real meals. A saloon where the whole family could sit simultaneously without anyone’s knees touching. Robin had arranged a vase of boat-friendly flowers, a personalized welcome card with every family member’s name, and cookies from a local bakery. We went back for more before departure, including gluten-free chocolate chip cookies…. Obviously.

bathroom with shower inside Simply Dreaming
saloon inside Simply Dreaming - blue U-shaped sofa with "live simply" pillows, a wooden table with flowers and cookies, and a flat-screen TV
stateroom inside Simply Dreaming - white bed with folded towels, wood paneling

Learning to Sail

Paul Miller teaching Jami Savage to sail a boat

Paul arrived Saturday morning, chill in the exact way Tracy had warned us he would be, and we spent the first part of the day on the dock going over lines, sails, and the basic vocabulary of sailing before casting off for Montague Harbour on Galiano Island. My son found the helm within the first hour and did not voluntarily leave it for the rest of the week. He arrived not knowing port from starboard. He left talking about buying a boat.

Young person in sunglasses and life vest steers a sailboat on a cloudy day with mountains in the background
Man in a life vest and cap operating a boat, with islands in the background

The teaching moment I keep returning to happened at Montague Harbour the following morning. Paul had us doing figure eights in the sheltered cove — a precision maneuver for building boat-handling confidence in close quarters. My husband and son both nailed it. Then Paul said: ‘Now do it backward.’ My husband nailed it again. My brain, for reasons that remain somewhat unclear to me, simply could not compute the task. I went through it extra times while my family watched with varying degrees of patience, and Paul let me work through the learning process on my own timeline without making it feel like anything other than part of the curriculum. That is teaching. That is the Skipper’s Mindset in its most ordinary and most instructive form.

My Daughter and the Dock

Girl in a life vest on a sailboat, forested islands under an overcast sky

On Day 3 at Ganges Marina, I docked the boat myself for the first time. Paul asked who wanted to take the helm for the approach, and my hand went up before I had consciously decided to raise it. I brought us in. I was genuinely, quietly proud, and I was proud that my kids were watching.

But the moment belongs to my daughter. Later the next day, Paul asked again, and she stepped up to the helm. She brought a 45-foot sailboat into a marina berth — first attempt, no assistance, at 17 years old. A dock worker watching the approach said to me: ‘I’m sure your captain’s got you.’ I said: ‘Yeah, that’s my kid bringing in this boat.’ His eyes went wide. My daughter was not especially fazed. Paul had built her confidence so thoroughly and so specifically that the docking felt, to her, like something she was simply ready to do. If there is a more precise demonstration of what great teaching looks like, I have not seen it.

Taco Night at Genoa Bay

Yellow and red-shingled Genoa Bay building on a wooden dock, with a marina sign, teal roofs, boats, and trees in the background

On Day 4, we chose our own destination — Genoa Bay, on the eastern shore of Cowichan Bay — and made tacos on the boat and played games well past bedtime. No iPads, no televisions, phones out only for the Bluetooth speaker with 80s music going. At some point my daughter went up to the dock washrooms and came back to tell us she could hear the family laughing from the top of the ramp. That is the soundtrack I want for every trip this family takes.

cambio card game spread on a white table with animal-themed cards, the game box, and a book

The next morning, my husband and son discovered that Genoa Bay Marina has a dockside breakfast operation run by a woman who opens massive wooden windows to reveal freshly baked cinnamon buns, banana bread too hot to cut, and egg sandwiches. They were there before it opened and still only got the last two cinnamon buns. We did not mourn the ones we missed. We were too busy eating the ones we had.

The Last Morning

Jami Savage in captain's hat and sunglasses on a boat, wearing a blue life vest, with men and mountains in background

We woke on our final morning in familiar water, and nobody was in a hurry. I was personally not in a hurry partly because the gentle motion of the boat had me sleeping four hours later than I normally do, and partly because I genuinely did not want it to end. My son was talking about the next charter before breakfast. My daughter had that quiet satisfaction of someone who knows what she did and does not need to announce it. My husband said the week exceeded his expectations in every way. I said the same, and I meant it in the specific sense that I had not quite known what this trip would be — and what it turned out to be was the best trip we have ever taken.

More Than a Vacation

Three people in a sailboat cockpit, with two standing and one seated, all wearing life vests
Jami Savage in red jacket and captain's hat steering a yacht in a marina, rope in foreground

The Transformational Travel Council — a global network of travel professionals and researchers — makes a distinction between travel that is consumptive and travel that is transformational: experiences that produce a shift in identity or capability that outlasts the trip itself. The difference is not about budget or destination or how many stars the hotel has. It is about active participation, stepping outside the familiar, and returning home genuinely different from who you arrived as.

That is the language I reach for when I try to explain this week. My son can sail. My daughter can dock a 45-foot boat. My family spent six days functioning as a high-performing team in conditions that actually required it — not in a metaphorical, trust-fall-exercise sense, but in the practical, consequential sense of a vessel that goes where you take it and does not offer a redo. That changes you. The confidence that builds when someone believes in you before you have the evidence to believe in yourself, as Paul demonstrated with my daughter at the helm, carries over into everything else. Tracy Sarich has watched it happen for years. She built a company specifically to produce it.

Three Women, One Industry

Jami Savage, Tracy Sarich, and Robin McKeown standing on sailboat "Simply Dreaming" docked in a marina under a cloudy sky, surrounded by other boats and water

Here is a thread worth pulling, because it ran through the entire week whether I named it or not. Adventure Awaits is a female-founded publication. Seaport Yacht Charters is female-owned and operated by the first woman in Canada to hold the Certified Marine Manager designation. Voyage Makers Coastal Adventures is female-founded and led by a woman who has spent years building female representation in the marine industry — at the Vancouver International Boat Show, where she produces the seminar programming and has grown the proportion of women speaking as experts from roughly 30 percent to more than 50 percent; in her Women’s Only Sail programs; in the network she is quietly assembling of women who are learning to sail, buying boats, and connecting with each other on the water.

Their joint backgrounder calls it plainly: two women-owned coastal companies. I would add a third. And I would add that the most eloquent expression of what all three represent happened not in any meeting or marketing material but on a dock in Ganges, Salt Spring Island, when a dock worker looked at the helm of a 45-foot sailboat and assumed a qualified adult must be steering it. It was my teenage daughter. She had been sailing for three days. The coast changes you, Tracy says. It also tends to show you, in the plainest possible terms, exactly who you are capable of being.

Ready to Plan Your Gulf Islands Sailing Adventure?

Sailing BC’s Gulf Islands Family Trip - Welcome Aboard sign on a yacht counter with a blue sofa, wooden table, flowers, and TV in the background

The two companion articles to this piece go deep into the specific experiences, companies, and people that made this week what it was. Start with whichever speaks to you first.

Seaport Yacht Charters Feature:Everything you need to know about Robin McKeown’s charter company — the boat, the fleet, the bareboat and instructional charter options, what’s included, and how to book. Read the full Seaport Yacht Charters article here.
Voyage Makers Coastal Adventures Feature:Everything you need to know about Tracy Sarich’s sailing school — the Skipper’s Mindset framework, Paul Miller, the day-by-day learning arc, and the wildlife you will encounter along the way. Read the full Voyage Makers article here.
Book Your Charter:Seaport Yacht Charters, Port Sidney Marina, Sidney, BC. seaportyachtcharters.com | [email protected]
Book Your Lessons:Voyage Makers Coastal Adventures, The Marina at Brentwood Bay Resort, 849 Verdier Avenue, Victoria, BC. Canada: 250-800-6001. US and WhatsApp: 206-949-6085. thevoyagemakers.com | [email protected]

Practical Information

Sailing BC’s Gulf Islands  Family Trip- white sailboat "Simply Dreaming" docked in a marina with blue water and sky

BC Ferries connects Tsawwassen (Metro Vancouver) to Swartz Bay in approximately 90 minutes; Port Sidney Marina is a 15-minute drive from the ferry terminal. Victoria International Airport is about 30 minutes from Port Sidney by car. Once you are aboard, the boat is your transportation for the week.

A minimum of six days to see Montague Harbour, Ganges, Genoa Bay, and Brentwood Bay without feeling rushed. Seven to ten days is better — every stop on this itinerary deserves more time than a one-night stay allows.

June through August for peak season conditions. May and September offer excellent sailing with fewer boats, lower rates, and often more attentive instruction in smaller groups. Pack layers regardless of the season — the water drops the apparent temperature significantly even on warm days.

Families at any experience level. Couples. Anyone who has ever said ‘I’ve always wanted to try sailing’ and kept finding reasons not to. Absolute beginners are genuinely welcome through the Seaport and Voyage Makers instructional charter partnership. No prior experience required. Bring your curiosity, your family, and your best layers. The Gulf Islands will handle the rest.

The Gulf Islands Are Waiting for You

Boats anchored in calm water with a treelined shore and power lines above

The question came at dinner on our last night at sea, and I answered it without pausing. 

The best trip I have ever taken was this one. Not the most remote. Not the most expensive. Not the one with the most photographs or the most recognizable destination. The one that asked the most of us and gave the most back. Six days on the water, watching my family figure out how to work as a crew, watching my daughter step back from a helm she had just brought a 45-foot boat into as if it were simply something she did now — because it was.

Seaport Yacht Charters and Voyage Makers Coastal Adventures have figured out something that most travel experiences do not even attempt: how to put you in conditions that genuinely require something of you, and then surround you with people skilled and generous enough to make sure you succeed. Robin McKeown built a company so that the boat is ready before you arrive and the welcome transition starts at the top of the ramp. 

Tracy Sarich built a school so that confidence is not something you perform but something you actually develop. Paul Miller spent five days making sure my family understood, in their bones, what they were capable of. These are not small things. They are, in the end, the whole thing.

The Gulf Islands are waiting. Your next adventure awaits!

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Jami Savage

An award-winning travel writer, TV personality, lifelong adventurer, mom, environmental advocate and unrelenting optimist, who started off as a humble Travel Blogger 11+ years ago! Learn more about me here.

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